CN105542508B - A kind of dispersion dyes monomer compound and its preparation method and application - Google Patents

A kind of dispersion dyes monomer compound and its preparation method and application Download PDF

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Publication number
CN105542508B
CN105542508B CN201610040024.9A CN201610040024A CN105542508B CN 105542508 B CN105542508 B CN 105542508B CN 201610040024 A CN201610040024 A CN 201610040024A CN 105542508 B CN105542508 B CN 105542508B
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monomer compound
application
added
compound
dispersion dyes
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CN105542508A (en
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俞杏英
姚晨华
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Zhejiang Wanfeng Chemical Co., Ltd
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俞杏英
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D06P3/143—Wool using dispersed dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/42—Cellulose acetate using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6033—Natural or regenerated cellulose using dispersed dyes
    • D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/72—Material containing nitrile groups using dispersed dyestuffs

Abstract

The present invention relates to a kind of dispersion dyes monomer compound and its preparation method and application, the structure of the compound is shown in formula I：Preparation method is prepared using diazotising, coupling reaction mode.The present invention, which is applied individually to any, to be prepared disperse dyes or prepares disperse dyes with other dye monomers composition dye composite.Preparation technology of the present invention is simple, and cost is low, for the dyestuff being prepared, has favorable reproducibility, water-fastness, rub resistance, the advantage of resistance to distillation, especially has and spell the characteristics of white fastness is high.

Description

A kind of dispersion dyes monomer compound and its preparation method and application
Technical field
The invention belongs to nonionic dye field, more particularly to a kind of dispersion dyes monomer compound and preparation method thereof And application.
Background technology
Disperse dyes are a kind of water-soluble relatively low nonionic dyes.Disperse dyes are used for the dye of acetate fiber earliest Color, referred to as cellulose acetate dye.With the development of synthetic fibers, polyamide fibre, terylene occur in succession, especially terylene, due to permutation Degree is high, and fiber gap is few, the characteristics such as hydrophobicity is strong.The fiber will make swelling of fiber under high temperature, thermosol, and dyestuff could enter fibre Dimension and upper dye.With the development of synthetic fibers, people it is also proposed new requirement to dyestuff, and there is conventional dyestuff application to lack Fall into, such as dye-uptake is low, fastness makes it difficult for people's receiving etc..In order to lift every fastness such as the washing of dyestuff, develop more Kind new dye.
A series of connection 2- oxoalkyl groups are disclosed in patent WO9520014, WO2005056690 and WO2008049758 The azo dispersion dyes of ester substitution, have excellent washability and splendid resistance to sublimability.But in other performances, such as sweat stain or spelling Defect is still suffered from white fastness, lacks broad applicability.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of dispersion dyes monomer compound and preparation method thereof and should With, compound preparation technology is simple, and cost is low, for the dyestuff being prepared, has a favorable reproducibility, water-fastness, rub resistance, The advantage of resistance to distillation, especially have and spell the characteristics of white fastness is high.
A kind of dispersion dyes monomer compound of the present invention, the structure of the compound is shown in formula I：
A kind of preparation method of dispersion dyes monomer compound of the present invention, comprises the following steps：
(1) aniline, acrylic acid, water are mixed, 90-100 DEG C of stirring reaction 20-24 hour, cooling, addition methanol, 0-5 DEG C Stir 12-18 hours；Filtering, water, soda ash and benzyl chloride are then added, mixed, KI, reaction are added at 80-100 DEG C 12-18 hours, cooling, methanol is added, 0-5 DEG C of stirring 12-18 hour, is mixed filter cake and DMF, soda ash and bromacetone after filtering Close, be warming up to 60-65 DEG C, add KI, stirring reaction 12-18 hours, be cooled to 40-45 DEG C, add water, filtering is esterified Thing；
(2) sulfuric acid and acetic acid are mixed, less than 10 DEG C addition 2- amino -3,5 dinitro thiophenes is dropped to, then at 0-5 DEG C Add nitrosyl sulfuric acid；After being added dropwise, diazotising liquid is obtained completely in 0-5 DEG C of stirring reaction 2-3 hour to reaction；
(3) carboxylate added in frozen water mixed liquor in sulfuric acid, sulfamic acid and step (1), step is added below 0 DEG C Suddenly the diazotising liquid in (2), stirring reaction 2-3 hours at 5-6 DEG C, filter, washing, dry and obtain compound.
A kind of application of dispersion dyes monomer compound of the present invention, the compound, which is applied individually to any, prepares disperse dyes Or prepare disperse dyes with other dye monomers composition dye composite.Composition refers to, according to printing color needs, incite somebody to action this Invention compound of formula I and other dye monomers are combined with arbitrary proportion.Described composition can also contain auxiliary agent.Composition can Using the printing and dyeing for different colours.
The preparation method of the disperse dyes is specially：By compound and auxiliary agent in mass ratio 1:0.8-5 is in water or wetting It is well mixed and grinds in the presence of agent, is then spray-dried, produced.
The auxiliary agent is one or both of dispersant, diffusant, surfactant.
The auxiliary agent be naphthalene sulfonic acid-formaldehyde condensation product, the resistance to sulfonic formaldehyde condensation compound of alkyl, benzyl naphthalene sulfonic acid-formaldehyde condensation product, One or both of lignosulfonates.Such as NNO, MF, CNF, Reax85A.
The disperse dyes are applied to dye hydrophobic material or blended material or stamp.
The hydrophobic material or blended material are acetate fiber, cotton, nylon, polyester fiber, acrylic fibers, wool or spandex.
The hydrophobic material or blended material can be thread, staple in bulk, yarn or woven or knitting fabric form.
Described disperse dyes can use common dip method, pad-dyeing method to print and dye, it can also be used to direct printing.Described printing and dyeing Method is this area conventional method.
Beneficial effect
Preparation technology of the present invention is simple, and cost is low, for the dyestuff being prepared, has favorable reproducibility, water-fastness, antifriction Wipe, the advantage of resistance to distillation, especially have and spell the characteristics of white fastness is high.
Brief description of the drawings
Fig. 1 is the one bath dyeing of formula (I) compound；
Fig. 2 is the H1-NMR spectrograms of formula (I) compound.
Embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention Rather than limitation the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, people in the art Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited Scope.
Embodiment 1
The preparation of carboxylate shown in formula (II)：
Aniline 37g, acrylic acid 28.8g, water 100g are mixed, 90 DEG C of stirring reactions 20 hours, cooling, add methanol 200g, 0 DEG C is stirred 12 hours, filtering, obtains the compound shown in formula (V).
By the compound 16g shown in formula (V), water 150g, soda ash 11g, benzyl chloride 20g mixing, stirring, iodine is added at 80 DEG C Change potassium 2g, react 12 hours, cooling, add methanol 100g, 0 DEG C is stirred 12 hours, filtering, obtains the compound shown in formula (IV).
By the compound and DMF 100g shown in 25.5g formulas (IV), soda ash 11g, bromacetone 14g mixing, 60 DEG C are warming up to, KI 1g is added, stirring reaction 12 hours, 40 DEG C is cooled to, adds water 200g, is filtered, obtains the carboxylate shown in formula (II).
The preparation of diazonium compound (III)：
Less than 40 DEG C mix 41.5g sulfuric acid and 9.5g acetic acid, drop to less than the 10 DEG C 2- for being slowly added into 4.65g amino- 3,5 dinitro thiophenes, then at 0 DEG C, it is slowly added into 8.2g nitrosyl sulfuric acids.After finishing after dripping, in 0 DEG C or so stirring reaction The 2 hours diazotising liquid obtained completely to reaction shown in formula (III).
Coupling reaction：
The ester shown in 2g sulfuric acid, 1.2g sulfamic acids and 7.8g formula (II) is added in the mixed liquor of 25g water and 50g ice Compound, is slowly added to above-mentioned diazotising liquid below 0 DEG C, stirring reaction 2 hours at 5 DEG C, filtering, and clear water washing, which is dried, to be obtained 10.68g formulas (I) compound.Fusing point：118℃-123℃.H1-NMR (deuterated DMSO) spectrogram is shown in Fig. 2.
Embodiment 2
After adding water to mix formula (I) compound 40g and MF 60g, with grinder grinding distribution, then it is spray-dried, Obtain blue dyes.
Embodiment 3
Disperse dyes made from 2.0g embodiments 2 are respectively taken, are made into the disperse dyes suspension that concentration is 2g/L respectively with water, 2ml is taken to be mixed with 8ml water, it is 5 to adjust dye bath pH with acetic acid, then heats to 60 DEG C, while be respectively put into 2g such as following table institutes The fibrous material shown carries out high-temperature pressure dyeing, and 130 DEG C are warming up in 30 minutes, is incubated 30 minutes, cools down, sampling.In detection Dye rate.And respectively according to the colour fastness to rubbing of national standard pertinent regulations testing example 2, washing color fastness, spell white fastness and Color fastness to sublimation.
It is as shown in the table, in washing fastness, crock fastness and spell white jail using disperse dyes made from the compounds of this invention Prior art is all significantly better than on degree.
As shown in figure 1, upper dye of the dyestuff of the present invention on fibrous material is all right, optimal upper dye temperature is 130 DEG C, It is adapted to conventional printing and dyeing condition.
Table 1
Table 2
Table 3

Claims (8)

  1. A kind of 1. dispersion dyes monomer compound, it is characterised in that：The structure of the compound is shown in formula I：
  2. 2. a kind of preparation method of dispersion dyes monomer compound, comprises the following steps：
    (1) aniline, acrylic acid, water are mixed, 90-100 DEG C of stirring reaction 20-24 hour, cooling, adds methanol, 0-5 DEG C of stirring 12-18 hours；Filtering, water, soda ash and benzyl chloride are then added, mixed, added KI at 80-100 DEG C, react 12- 18 hours, cooling, methanol is added, 0-5 DEG C of stirring 12-18 hour, is mixed filter cake and DMF, soda ash and bromacetone after filtering, 60-65 DEG C is warming up to, KI is added, stirring reaction 12-18 hours, is cooled to 40-45 DEG C, adds water, filtering obtains carboxylate；
    (2) sulfuric acid and acetic acid are mixed, less than 10 DEG C addition 2- amino -3,5 dinitro thiophenes is dropped to, then in 0-5 DEG C of addition Nitrosyl sulfuric acid；After being added dropwise, diazotising liquid is obtained completely in 0-5 DEG C of stirring reaction 2-3 hour to reaction；
    (3) carboxylate added in frozen water mixed liquor in sulfuric acid, sulfamic acid and step (1), step is added below 0 DEG C (2) the diazotising liquid in, stirring reaction 2-3 hours at 5-6 DEG C, filter, washing, dry and obtain compound.
  3. A kind of 3. application of dispersion dyes monomer compound as claimed in claim 1, it is characterised in that：The compound is independent Disperse dyes are prepared applied to preparing disperse dyes or forming dye composite with other dye monomers.
  4. A kind of 4. application of dispersion dyes monomer compound according to claim 3, it is characterised in that：The disperse dyes Preparation method be specially：By compound and auxiliary agent in mass ratio 1:0.8-5 is well mixed simultaneously in the presence of water or wetting agent Grinding, is then spray-dried, is produced.
  5. A kind of 5. application of dispersion dyes monomer compound according to claim 4, it is characterised in that：The auxiliary agent is point One or both of powder, diffusant.
  6. A kind of 6. application of dispersion dyes monomer compound according to claim 4, it is characterised in that：The auxiliary agent is naphthalene One in sulfonic formaldehyde condensation compound, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic acid-formaldehyde condensation product, lignosulfonates Kind or two kinds.
  7. A kind of 7. application of dispersion dyes monomer compound according to claim 3, it is characterised in that：The disperse dyes Applied to being dyed to hydrophobic material or blended material or stamp.
  8. A kind of 8. application of dispersion dyes monomer compound according to claim 7, it is characterised in that：The hydrophobicity material Material or blended material are acetate fiber, nylon, polyester fiber, acrylic fibers or spandex.
CN201610040024.9A 2016-01-20 2016-01-20 A kind of dispersion dyes monomer compound and its preparation method and application Active CN105542508B (en)

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Publication number Priority date Publication date Assignee Title
CN106675083A (en) * 2016-12-16 2017-05-17 江苏道博化工有限公司 Synthetic method for disperse yellow 231

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GB909843A (en) * 1959-02-10 1962-11-07 Ici Ltd New monoazo dyestuffs containing ester groups
GB9400972D0 (en) * 1994-01-19 1994-03-16 Zeneca Ltd Process
TWI352103B (en) * 2003-12-10 2011-11-11 Clariant Finance Bvi Ltd Disperse dyes
DE102006050642A1 (en) * 2006-10-27 2008-04-30 Dystar Textilfarben Gmbh & Co. Deutschland Kg New azo dyes with a 2-oxoalkyl ester unit attached to the chromophore, used for dyeing and printing hydrophobic materials, e.g. for digital textile printing by the ink-jet process
CN102816453B (en) * 2012-07-10 2015-05-20 浙江龙盛集团股份有限公司 Disperse dye monomeric compound and disperse dye

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